Ciprofloxacin → 1-Cyclopropyl-6-fluoro-1,4-dihydro-7-[4-(5-methyl-2-oxo-1,3-dioxol-4-yl-methyl)-1-piperazinyl]-4-oxo-3-quinolinecarboxylic acid

HRID 256315

Reaktionsgleichung

Reaktionsgleichung von HRID 256315
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:20])=[C:11]([N:14]4[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]4)[CH:12]=3)[C:7](=[O:21])[C:6]([C:22]([OH:24])=[O:23])=[CH:5]2)[CH2:3][CH2:2]1.Br[CH2:26][C:27]1[O:28][C:29](=[O:33])[O:30][C:31]=1[CH3:32].C(=O)(O)[O-].[K+]>CN(C)C=O>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:20])=[C:11]([N:14]4[CH2:19][CH2:18][N:17]([CH2:26][C:27]5[O:28][C:29](=[O:33])[O:30][C:31]=5[CH3:32])[CH2:16][CH2:15]4)[CH:12]=3)[C:7](=[O:21])[C:6]([C:22]([OH:24])=[O:23])=[CH:5]2)[CH2:2][CH2:3]1

Komponenten

5

Edukt 3

HCID 2764CiprofloxacinHCID 516893Potassium BicarbonateHCID 107741414-(Bromomethyl)-5-methyl-1,3-dioxol-2-one

Produkt 1

HCID 136732721-Cyclopropyl-6-fluoro-1,4-dihydro-7-[4-(5-methyl-2-oxo-1,3-dioxol-4-yl-methyl)-1-piperazinyl]-4-oxo-3-quinolinecarboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1.15 g (3.5 mmoles) of 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid are stirred in 20 ml of dimethylformamide with 0.85 g (4.4 mmoles) of 4-bromomethyl-5-methyl-1,3-dioxol-2-one and 0.42 g (4.2 mmoles) of powdered potassium bicarbonate for 3 days, while cooling with ice. The mixture is concentrated in vacuo, the residue is stirred with 20 ml of water, the resulting greasy product is dissolved in methanol and the solution is filtered. The filtrate is left to stand at room temperature for 2 days and the colorless crystals which have precipitated are isolated.

Aufarbeitung

  1. temperaturewhile cooling with ice
  2. concentrationThe mixture is concentrated in vacuo
  3. dissolutionthe resulting greasy product is dissolved in methanol
  4. filtrationthe solution is filtered
  5. waitThe filtrate is left
  6. customthe colorless crystals which have precipitated
  7. customare isolated

Quellen und Nachweise

ORD-Eintrag
ord-a73071cede0544c8b4b53d87ab259d7d
Quelldatensatz
uspto-grants-1987_10
Patentnummer
US04703047

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